The bis-tetrahydroisoquinoline (bis-THIQ) family of natural products has been studied intensively in the 40 years since their initial discovery. This family of molecules is highlighted by exceptionally potent anticancer activity in addition to strong gram-positive and gram-negative antibiotic character. Jorumycin is considered the minimum pharmacophore of this natural product family, possessing a pentacyclic core, polyoxygenated termini, and carbinolamine functionality that lend these natural products their marked biological activity. To date, existing synthetic strategies toward the bis-THIQ natural products have relied heavily on electrophilic aromatic chemistry, such as the Pictet-Spengler reaction, which has limited the synthesis of non-natural analogs to highly electron-rich species that facilitate this reactivity. Accordingly, there is a need to develop new routes to access jorumycin and related analogs in the bis-THIQ family of natural products which have a full range of electrophilicity in substituents on the pentacyclic core, including electron deficient analogs.